Reacción #1552042

Ecuación de reacción

N-acetylphenylalanine 2-(phenylseleno)ethyl ester

H2O2

→

N-acetylphenylalanine vinyl ester

Disolventes

CHCl3

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring the mixture for 12 hours at room temperature
2. 2
   Extracciónextracted with 3×50 ml of water
3. 3
   SecadoThe organic phases were then dried over sodium sulfate
4. 4
   Otrothe solvent was removed
5. 5
   Temperaturawas refluxed for 24 hours
6. 6
   TemperaturaAfter cooling
7. 7
   Otrothe solvent was removed
8. 8
   OtroFlash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid

Procedimiento

To a solution of 2.6 g (6.66 mmol) of N-acetylphenylalanine 2-(phenylseleno)ethyl ester in 20 ml of THF, 8 ml of a 30% H2O2 solution were added dropwise within 10 minutes at 0° C., and the solution was stirred at 0° C. for another 30 minutes. After stirring the mixture for 12 hours at room temperature, it was diluted with 80 ml of CHCl3 and extracted with 3×50 ml of water. The organic phases were then dried over sodium sulfate, and the solvent was removed. The residue was taken up in 70 ml of chloroform and was refluxed for 24 hours. After cooling, the solvent was removed. Flash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid.

Fuente